This invention pertains generally to organic synthesis and in particular to organic synthesis with isomeric exclusively.
Trifluoromethanesulfonates are often referred to as triflates. The term will also be used hereinafter for trifluoromethanesulfonate.
Alkyl perchlorates and triflates are excellent alkylating agents for weakly nucleophilic compounds such as amines, alcohols, and nitroalcohols. Numerous methods are known for the preparation of perchlorate compounds. Examplary of the known perchlorate synthesis are the reaction of as alkyl halide with silver perchlorate in carbon tetrachloride or heptane, the reaction of barium alkyl sulfate with barium perchlorate, the reaction of diazomethane with perchloric acid, and the reaction disclosed in U.S. Pat. No. 3,660,455. All of the cited reactions produced either an isomer other than the primary configuration or produced a mixture of isomers. The only known method of producing a primary alkyl perchlorate is disclosed in Baum and Beard. Reactions of Dichlorine Heptoxide with Alcohols. in J. Amer. Chem. Soc. 96:10. p. 3233-3237 (May 15, 1974). This method, however, has the disadvantages of being slightly difficult and expensive.
Much less is known concerning the preparation of alkyl triflates. The most versatile and practical method is disclosed in patent application Ser. No. 515,383, filed on Oct. 16, 1974, by Kurt Baum and Charles D. Beard. While the method, unlike the other known methods, is able to produce alkyl triflates greater than ethyl triflate, this method is also slightly difficult and expensive in that an anhydride is prepared.